Pyrrolopyrrole Aza‐BODIPY Analogues as Near‐Infrared Chromophores and Fluorophores: Red‐Shift Effects of Substituents on Absorption and Emission Spectra

Kage, Yuto; Karasaki, Hideaki; Mori, Shigeki; Furuta, Hiroyuki; Shimizu, Soji

doi:10.1002/cplu.201900226

Cited by 23 publications

(11 citation statements)

References 43 publications

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“…Four-coordinate organoboron compounds with the rigid ligand often show good photoluminescence (PL) quantum yields and high hole and/or electron mobility. − Boron coordination can improve molecular rigidity and planarity which lead to functional luminescent materials. The coordination potentially lowers the energy level of the lowest unoccupied molecular orbital (LUMO) because of the interaction between a lone pair of a nitrogen atom and a vacant p-orbital of a boron atom. , Kawashima et al reported that by forming a N–B coordination with azobenzene, the resulting complexes showed intense fluorescence. − It is clarified that fluorescence can be induced by intramolecular N–B interaction which inhibits photoisomerization at the azobenzene scaffold and allowed the electronic transition related to emission.…”

Section: Introductionmentioning

confidence: 99%

Near-Infrared Absorptive and Emissive Poly(p-phenylene vinylene) Derivative Containing Azobenzene–Boron Complexes

et al. 2020

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Poly(p-phenylene vinylene) (PPV) is known to be a typical π-conjugated polymer and used as a commodity platform for constructing optoelectronic organic devices because of superior optical and material properties. PPV derivatives generally show a large degree of light absorption and intense emission in the visible region; meanwhile, very few examples have been reported to offer near-infrared (NIR) absorptive and emissive PPV derivatives. In this study, we designed and synthesized a novel PPV derivative, named BAz-PPV, containing boron-fused NN double bond units in the main chain. BAz-PPV showed intense NIR absorption and emission (λabs = 702 nm, λPL = 760 nm, and ΦPL = 2.0% in diluted toluene). This polymer had a narrow energy band gap because of not only extension of main chain π-conjugation over 50 monomer units but also stabilization of the energy level of the lowest unoccupied molecular orbital. Moreover, the polymer shows high stability toward photodegradation and sufficient carrier-transport ability for the applications in organic semiconducting devices. Advantages of the introduction of the NN double bond to main-chain conjugation followed by boron coordination for the development of NIR materials are demonstrated in this manuscript.

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Section: Introductionmentioning

confidence: 99%

Near-Infrared Absorptive and Emissive Poly(p-phenylene vinylene) Derivative Containing Azobenzene–Boron Complexes

et al. 2020

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“…The corresponding excitation peak has also changed (Figure S11). Similarly, the absorption of Cu-Pc-CDs in the Soret band at 370 nm is redshifted (about 45 nm) compared with that of Cu-Pc, demonstrating the formation of new chromophores (Figure e) . What is particularly interesting is that the Q absorption band at the visible-light region (732 nm) disappears, avoiding light absorption losses of the PVK layer .…”

Section: Resultsmentioning

confidence: 86%

The Insolubility Problem of Organic Hole-Transport Materials Solved by Solvothermal Technology: Toward Solution-Processable Perovskite Solar Cells

Yao

Kong

Shi

et al. 2022

ACS Appl. Mater. Interfaces

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Generally, the high efficiency of solution-processable perovskite solar cells (PSCs) comes at the expense of using expensive organic matters as a hole-transport material (HTM). Although intense efforts have tried to use commercially available and low-cost macrocyclic molecules as HTM candidates, they still face two enormous challenges: poor solubility and inherent instability. Here, solvothermal treatment for old and insoluble HTMs (phthalocyanine (Pc) and its derivatives) has been proposed, which is unusual due to the occurrence of solubilization for insoluble precursors induced by the carbonization of the dissolved part. Since the macrocyclic structure still exists, the as-prepared new-type carbon dots not only retain the capacity of hole transfer but serve as an effective passivation additive. Synergy makes the all-air-processed carbon-based PSCs (CH3NH3PbI3) fabricated with carbon dots achieve a decent power conversion efficiency of 13.7%. Importantly, organics have undergone solvothermal treatment, completely breaking through the instability bottleneck, which exists in the long-term operation of PSCs. The universality of this methodology will usher exploration into other low-cost insoluble organics and drastically enhance the high-performance cost ratio of PSC equipment.

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“…Further elongating the thienyl numbers at the α‐positions to red‐shift absorption was demonstrated in their later report. [ 126 ] Moreover, upon cutting the fused heterocycles and the α‐aromatic substituents, significantly changed energy levels and bandgaps were observed. It worth to note that these B‐complexed DPP molecules (63‐70) showed low‐lying LUMOs of −3.8–−3.5 eV, suggesting strong electron affinity and potential electron‐transport properties.…”

Section: B←n‐bridged Conjugated Unitsmentioning

confidence: 99%

B←N Coordination: From Chemistry to Organic Photovoltaic Materials

Huang

Wang

Xiang

et al. 2021

Adv Energy and Sustain Res

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Coordination between boron Lewis acid and nitrogen Lewis base (B←N) is a classically chemical issue that has been known for several decades. Recently, this B←N chemistry developed into a new stage toward electronic materials, e.g., adjusting optoelectronic properties of N‐based conjugated molecules via adding B Lewis acids, synthesizing B←N‐bridged conjugated units, and further constructing B←N‐embedded organic photovoltaic (OPV) materials. Herein, these progresses are systematically summarized starting from certain chemical issues concerning B←N coordination, e.g., Lewis acidity of typical B Lewis acids and their interactions with N‐contained conjugated molecules. Then, some fused and ladder‐type B←N‐bridged units are reviewed in terms of the relationship between molecular structures and optoelectronic properties. Finally, the recently flourished B←N‐embedded OPV materials are summarized. The prospect of OPV materials concerning B←N coordination is also proposed, hoping to attract more attention to this filed and motivate its rolling rapidly.

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Pyrrolopyrrole Aza‐BODIPY Analogues as Near‐Infrared Chromophores and Fluorophores: Red‐Shift Effects of Substituents on Absorption and Emission Spectra

Cited by 23 publications

References 43 publications

Near-Infrared Absorptive and Emissive Poly(p-phenylene vinylene) Derivative Containing Azobenzene–Boron Complexes

Near-Infrared Absorptive and Emissive Poly(p-phenylene vinylene) Derivative Containing Azobenzene–Boron Complexes

The Insolubility Problem of Organic Hole-Transport Materials Solved by Solvothermal Technology: Toward Solution-Processable Perovskite Solar Cells

B←N Coordination: From Chemistry to Organic Photovoltaic Materials

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